benzyl [1,1'-biphenyl]-4-carboxylate | 71945-53-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzyl [1,1'-biphenyl]-4-carboxylate
• 英文别名: benzyl [1,1’-biphenyl]-4-carboxylate；Benzyl-p-phenyl-benzoat；Benzyl 4-phenylbenzoate
• CAS: 71945-53-4
• 化学式: C₂₀H₁₆O₂
• 分子量: 288.346
• InChiKey: FLYIMCRIZNIKLD-UHFFFAOYSA-N

物化性质

• 沸点：
  447.8±24.0 °C(Predicted)
• 密度：
  1.138±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  对苯基苯甲醛 在 4-二甲氨基吡啶 、 N-氯代丁二酰亚胺 、 9-噻吨酮 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 23.0h， 生成 benzyl [1,1'-biphenyl]-4-carboxylate
  参考文献：
  名称：

  芳香醛的光化学活化：酰胺，异羟肟酸和酯的合成

  摘要：

  已经开发了用于芳族醛活化的便宜，容易且无金属的光化学方案。利用噻吨酮-9-one作为光催化剂，使用廉价的家用灯作为光源，已活化了多种芳香醛，然后通过一锅法将其转化为酰胺，异羟肟酸和酯，产率高至高。该方法的适用性在抗抑郁和社交焦虑药物莫氯贝胺的合成中得到了强调。为了确定该反应的合理机制，已经进行了详细的机理研究。

  DOI：

  10.1002/chem.202100655

文献信息

• Copper-Catalyzed Synthesis of Esters from Ketones. Alkyl Group as a Leaving Group
  作者：Yuji Nakatani、Yuichiro Koizumi、Ryu Yamasaki、Shinichi Saito

  DOI：10.1021/ol800576w

  日期：2008.5.1

  The conversion of ketones to esters has been achieved through the use of Cu catalyst and tetrabutylammonium nitrite. This reaction involves the activation of the less activated C-C bond, and the alkyl group is removed as a leaving group. Various isopropyl ketones are found to be good substrates for this reaction.

  通过使用铜催化剂和亚硝酸四丁铵，已将酮转化为酯。该反应涉及活化程度较低的CC键的活化，并且烷基作为离去基团被除去。发现各种异丙基酮是该反应的良好底物。
• Reusable ionic liquid-catalyzed oxidative esterification of carboxylic acids with benzylic hydrocarbons via benzylic Csp³–H bond activation under metal-free conditions
  作者：Fen Mou、Yadong Sun、Weiwei Jin、Yonghong Zhang、Bin Wang、Zhiqing Liu、Lei Guo、Jianbin Huang、Chenjiang Liu

  DOI：10.1039/c7ra02788e

  日期：——

  A metal-free protocol for the direct oxidative esterification of the Csp3–H bond in benzylic hydrocarbons with carboxylic acids using heterocyclic ionic liquid as catalyst has been reported. The catalyst 1-butylpyridinium iodide could be easily recycled and reused for at least four cycles without obvious loss of catalytic activity.

  已经报道了使用杂环离子液体作为催化剂的无金属方案，可用于苄基烃中的Csp 3 -H键与羧酸的直接氧化酯化反应。催化剂碘化1-丁基吡啶鎓可以很容易地再循环和再利用至少四个循环，而没有明显的催化活性损失。
• <i>N</i> -Methylpyrrolidin-2-one-Promoted Formation of Functional Esters through C-O Bond Cleavage
  作者：Jianming Liu、Yanyan Wang、Yuanyuan Yue、Na Liu、Jian Zhang、Shufang Zhao、Qinghu Tang、Kelei Zhuo

  DOI：10.1002/ejoc.201700514

  日期：2017.5.10

  catalyzed C–O bond cleavage leading to the preparation of functional esters in the presence of N-methylpyrrolidin-2-one (NMP) was accomplished. Various substrates were well tolerated, and a gram-scale experiment was successfully realized. DFT calculations indicated that NMP plays a decisive role in accelerating nucleophilic attack of the functional acid to generate the functional esters in chlorobenzene

  三氟甲磺酸催化的 C-O 键断裂导致在 N-甲基吡咯烷-2-酮 (NMP) 存在下制备功能性酯。各种底物均具有良好的耐受性，并成功实现了克级实验。DFT 计算表明 NMP 在加速功能酸的亲核攻击以在氯苯中生成功能酯方面起着决定性作用。
• Palladium-Catalyzed Carbonylative Synthesis of Benzyl Benzoates Employing Benzyl Formates as Both CO Surrogates and Benzyl Alcohol Sources
  作者：Ming Lai、Xinxin Qi、Xiao-Feng Wu

  DOI：10.1002/ejoc.201900700

  日期：2019.6.23

  An efficient and convenient palladium‐catalyzed carbonylation reaction for the synthesis of benzyl benzoates from aryl bromides has been developed. Benzyl formates have been explored as a new type of efficient and useful CO sources. A wide range of benzyl benzoates were obtained in good to excellent yields.

  已经开发了一种有效且方便的钯催化羰基化反应，用于从芳基溴化物合成苯甲酸苄酯。苄基甲酸酯已被研究为一种新型的高效有用的CO来源。以良好至优异的产率获得了多种苯甲酸苄酯。
• Highly Selective and Efficient Catalyst for Carbonylation of Aryl Iodides:Dimeric Palladium Complex Containing Carbon-Palladium Covalent Bond
  作者：Yoshihiro Sugi、Chinnasamy Ramesh、Yoshihiro Kubota、Minoru Miwa

  DOI：10.1055/s-2002-34836

  日期：——

  Dimeric cyclometallated oxime palladium complex containing palladium-carbon covalent bond was found to efficiently catalyze the carbonylation reactions of aryl iodides with various alcohols to give esters in excellent yields with high selectivity. These complexes were also stable under a carbon monoxide atmosphere at high temperatures.

  发现含有钯-碳共价键的二聚环金属肟钯配合物可有效催化芳基碘化物与各种醇的羰基化反应，以优异的收率和高选择性得到酯。这些配合物在高温下在一氧化碳气氛下也是稳定的。